Bis[2-meth­oxy-6-(phenyl­iminiomethyl)phenolate-κ2O,O′]bis­(thio­cyanato-κN)manganese(II)

Shen, J.-B.; Ge, G.-D.; Zhao, G.-L.

doi:10.1107/S1600536811009330

metal-organic compounds

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Volume 67| Part 4| April 2011| Page m463

doi:10.1107/S1600536811009330

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Bis[2-methoxy-6-(phenyliminiomethyl)phenolate-κ²O,O′]bis(thiocyanato-κN)manganese(II)

Jin-Bei Shen,^a Guo-Di Ge ^a and Guo-Liang Zhao ^a,^b ^*

^aCollege of Chemistry and Life Science, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China, and ^bXingzhi College, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: sky53@zjnu.cn

(Received 10 March 2011; accepted 11 March 2011; online 19 March 2011)

The Mn^II atom in the title complex, [Mn(NCS)₂(C₁₄H₁₃NO₂)₂], lies on a center of inversion in a MnO₄N₂ octahedral geometry. The Schiff base is present in its zwitterionic form and is O,O′-chelated to the metal atom. The imino N atom is protonated and is involved in an intramolecular hydrogen bond with the phenolate O atom.

Related literature

For Schiff base ligands derived from o-vanillin and aniline and their rare earth complexes, see: Li et al. (2008 ); Liu et al. (2009 ); Xian et al. (2008 ); Zhao et al. (2005 , 2007 ).

Experimental

Crystal data

[Mn(NCS)₂(C₁₄H₁₃NO₂)₂]
M_r = 625.61
Triclinic, $[P \overline 1]$
a = 9.0204 (2) Å
b = 9.3070 (2) Å
c = 9.4087 (2) Å
α = 87.417 (1)°
β = 82.010 (1)°
γ = 65.693 (1)°
V = 712.81 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 296 K
0.29 × 0.17 × 0.05 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.877, T_max = 0.970
9483 measured reflections
2509 independent reflections
2233 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.077
S = 1.06
2509 reflections
188 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	1.97	2.6501 (16)	135

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009330/ng5130sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009330/ng5130Isup2.hkl

checkCIF report

Comment top

For many years, there has been considerable interest in the study of Schiff base compounds due to their biological activity (Zhao et al., 2005). Interested in this field, we have been synthesized several analogous Schiff bases derived from o-vanillin and prepared their transitional and rare metal complexes further. In a few of articles we have reported our partial research results (Zhao et al., 2007; Xian et al. 2008; Li et al. 2008; Liu et al. 2009). Herein, we describe a new Mn(II) complex.

The structure of complex (1) was shown in Fig. 1 and the coordination environment of Mn(II) was shown in Fig. 2. In this complex the Mn(II) is six- coordinated by two N atoms from thiocyanate ions and four O atoms from the Schiff bases (HL), which can be described as a distorted octahedral geometry. There thiocyanate anions coordinate to Mn(II) ion with N atoms occupying the apices and two HL ligands chelate the Mn(II) ion with four O atoms from deprotonated phenol groups and methoxyl groups occupying the equatorial positions. The Mn—O and Mn—N bond distances were listed in Table 1, The distances between Mn(II) and methoxyl O atoms are obvious longer than Mn—O(phenolic) bond distances, which are similar to the analogous complexes (Zhao et al., 2007; Li et al., 2008, Liu et al., 2009).

The hydrogen bonds and π–π weak non-covalent interactions lend stability to the structure. The stacking plot of this compound was shown in Fig. 3. In HL ligand, two protons of phenolic hydroxyl groups considered to have transferred to imine N atoms involve in forming intramolecular hydrogen bonds. The π–π interactions exist both intra and extra molecules between the approximate paralleled participating benzene rings, which may be the primary forces keep the complex molecules packing together.

Related literature top

For Schiff base ligands derived from o-vanillin and aniline and their rare earth complexes, see: Li et al. (2008); Liu et al. (2009); Xian et al. (2008); Zhao et al. (2005); Zhao et al. (2007).

Experimental top

Reagents and solvents used were of commercially available quality and without purified before using. The Schiff base ligand 2-(phenyliminomethyl)-6-methoxyphenol was synthesized from condensation of o-vanillin and aniline. The title compound was synthesized by traditional method. 1 mmol HL ligand was dissolved in ethanol, then 0.5 mmol Mn(NO₃)₂.6H₂O (in ethanol) was added to the upper solution. The mixture solution was stirred for 2 h at room temperature. Furthermore, 1 mmol NH₄SCN (dissolved in ethanol) was added. The mixture was stirred again for 8 h at room temperature. At last, deposit was filtered out and the reddish-brown solution was kept in the open air. The red crystal was obtained after several days.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The coordination environment of the Mn(II).
	Fig. 3. The stacking plot of the title compound, showing H-bond interactions (dashed lines) and π–π stacking interactions.

Bis[2-methoxy-6-(phenyliminiomethyl)phenolate- κ²O,O']bis(thiocyanato-κN)manganese(II) top

Crystal data top

[Mn(NCS)₂(C₁₄H₁₃NO₂)₂]	Z = 1
M_r = 625.61	F(000) = 323
Triclinic, P1	D_x = 1.457 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0204 (2) Å	Cell parameters from 4271 reflections
b = 9.3070 (2) Å	θ = 2.2–25.0°
c = 9.4087 (2) Å	µ = 0.65 mm⁻¹
α = 87.417 (1)°	T = 296 K
β = 82.010 (1)°	Block, red
γ = 65.693 (1)°	0.29 × 0.17 × 0.05 mm
V = 712.81 (3) Å³

Data collection top

Bruker APEXII area-detector diffractometer	2509 independent reflections
Radiation source: fine-focus sealed tube	2233 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.877, T_max = 0.970	k = −11→11
9483 measured reflections	l = −11→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0423P)² + 0.1242P] where P = (F_o² + 2F_c²)/3
2509 reflections	(Δ/σ)_max = 0.001
188 parameters	Δρ_max = 0.17 e Å⁻³
2 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Mn(NCS)₂(C₁₄H₁₃NO₂)₂]	γ = 65.693 (1)°
M_r = 625.61	V = 712.81 (3) Å³
Triclinic, P1	Z = 1
a = 9.0204 (2) Å	Mo Kα radiation
b = 9.3070 (2) Å	µ = 0.65 mm⁻¹
c = 9.4087 (2) Å	T = 296 K
α = 87.417 (1)°	0.29 × 0.17 × 0.05 mm
β = 82.010 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	2509 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2233 reflections with I > 2σ(I)
T_min = 0.877, T_max = 0.970	R_int = 0.022
9483 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	2 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.06	Δρ_max = 0.17 e Å⁻³
2509 reflections	Δρ_min = −0.24 e Å⁻³
188 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Mn1	0.0000	0.5000	0.5000	0.03697 (13)
S1	0.00911 (6)	0.11697 (6)	0.14672 (6)	0.05653 (16)
O1	0.24701 (13)	0.46530 (13)	0.41948 (12)	0.0385 (3)
N1	0.48105 (16)	0.51194 (15)	0.24678 (14)	0.0354 (3)
H1A	0.3779	0.5397	0.2737	0.043*
O2	0.16157 (14)	0.30666 (15)	0.63303 (13)	0.0465 (3)
C7	0.36297 (19)	0.35112 (18)	0.47429 (16)	0.0320 (3)
C13	0.32723 (19)	0.25949 (19)	0.58901 (17)	0.0361 (4)
C9	0.53201 (19)	0.31088 (19)	0.42564 (17)	0.0354 (4)
C15	0.01407 (19)	0.2348 (2)	0.26679 (19)	0.0401 (4)
C8	0.58045 (19)	0.3952 (2)	0.31424 (18)	0.0389 (4)
H8A	0.6924	0.3648	0.2870	0.047*
C4	0.5244 (2)	0.59880 (19)	0.13313 (17)	0.0358 (4)
C3	0.6852 (2)	0.5520 (2)	0.06908 (19)	0.0451 (4)
H3A	0.7678	0.4615	0.0990	0.054*
C12	0.4481 (2)	0.1394 (2)	0.64754 (19)	0.0452 (4)
H12A	0.4207	0.0812	0.7213	0.054*
C5	0.4016 (2)	0.7315 (2)	0.08693 (19)	0.0441 (4)
H5A	0.2935	0.7612	0.1290	0.053*
C2	0.7210 (2)	0.6418 (2)	−0.0399 (2)	0.0537 (5)
H2A	0.8288	0.6114	−0.0832	0.064*
N2	0.01391 (19)	0.3211 (2)	0.35072 (18)	0.0554 (4)
C10	0.6546 (2)	0.1866 (2)	0.4902 (2)	0.0475 (4)
H10A	0.7647	0.1625	0.4585	0.057*
C1	0.5992 (3)	0.7757 (2)	−0.0853 (2)	0.0551 (5)
H1B	0.6248	0.8357	−0.1583	0.066*
C11	0.6141 (2)	0.1025 (2)	0.5974 (2)	0.0514 (5)
H11A	0.6960	0.0202	0.6380	0.062*
C6	0.4396 (2)	0.8202 (2)	−0.0220 (2)	0.0529 (5)
H6A	0.3570	0.9103	−0.0526	0.063*
C14	0.1088 (3)	0.2163 (3)	0.7377 (3)	0.0723 (7)
H14A	0.1511	0.2175	0.8256	0.108*
H14B	0.1487	0.1096	0.7035	0.108*
H14C	−0.0089	0.2609	0.7546	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.02590 (19)	0.0477 (2)	0.0377 (2)	−0.01664 (16)	−0.00189 (14)	0.00535 (15)
S1	0.0503 (3)	0.0525 (3)	0.0652 (3)	−0.0210 (2)	0.0012 (2)	−0.0120 (2)
O1	0.0265 (6)	0.0450 (7)	0.0419 (6)	−0.0142 (5)	−0.0032 (5)	0.0135 (5)
N1	0.0272 (7)	0.0401 (8)	0.0386 (7)	−0.0153 (6)	0.0018 (6)	0.0017 (6)
O2	0.0352 (6)	0.0583 (8)	0.0466 (7)	−0.0229 (6)	−0.0025 (5)	0.0208 (6)
C7	0.0309 (8)	0.0344 (8)	0.0321 (8)	−0.0152 (7)	−0.0033 (6)	0.0011 (6)
C13	0.0345 (9)	0.0419 (9)	0.0347 (8)	−0.0188 (7)	−0.0038 (7)	0.0027 (7)
C9	0.0306 (8)	0.0381 (9)	0.0355 (8)	−0.0132 (7)	−0.0018 (6)	0.0021 (7)
C15	0.0272 (8)	0.0426 (10)	0.0477 (10)	−0.0136 (7)	0.0009 (7)	0.0048 (7)
C8	0.0263 (8)	0.0460 (10)	0.0418 (9)	−0.0139 (7)	0.0010 (7)	0.0012 (7)
C4	0.0367 (9)	0.0379 (9)	0.0359 (8)	−0.0199 (7)	0.0000 (7)	−0.0004 (7)
C3	0.0359 (9)	0.0495 (11)	0.0469 (10)	−0.0175 (8)	0.0016 (8)	0.0083 (8)
C12	0.0488 (11)	0.0445 (10)	0.0409 (9)	−0.0184 (8)	−0.0078 (8)	0.0120 (8)
C5	0.0382 (10)	0.0441 (10)	0.0468 (10)	−0.0154 (8)	−0.0008 (8)	0.0022 (8)
C2	0.0426 (10)	0.0636 (12)	0.0546 (11)	−0.0263 (10)	0.0068 (9)	0.0085 (9)
N2	0.0465 (9)	0.0663 (11)	0.0562 (10)	−0.0280 (8)	0.0035 (8)	−0.0098 (8)
C10	0.0306 (9)	0.0516 (11)	0.0512 (11)	−0.0089 (8)	−0.0038 (8)	0.0063 (8)
C1	0.0620 (13)	0.0575 (12)	0.0500 (11)	−0.0318 (11)	−0.0014 (9)	0.0142 (9)
C11	0.0422 (10)	0.0481 (11)	0.0531 (11)	−0.0073 (8)	−0.0115 (8)	0.0139 (9)
C6	0.0541 (12)	0.0450 (11)	0.0542 (11)	−0.0160 (9)	−0.0076 (9)	0.0124 (9)
C14	0.0556 (13)	0.0807 (16)	0.0782 (15)	−0.0333 (12)	0.0049 (11)	0.0363 (12)

Geometric parameters (Å, º) top

Mn1—O1	2.1455 (10)	C4—C5	1.379 (2)
Mn1—O1ⁱ	2.1455 (10)	C4—C3	1.384 (2)
Mn1—N2	2.1794 (16)	C3—C2	1.381 (2)
Mn1—N2ⁱ	2.1794 (16)	C3—H3A	0.9300
Mn1—O2	2.2525 (12)	C12—C11	1.406 (3)
Mn1—O2ⁱ	2.2525 (12)	C12—H12A	0.9300
S1—C15	1.6270 (19)	C5—C6	1.381 (3)
O1—C7	1.2942 (19)	C5—H5A	0.9300
N1—C8	1.297 (2)	C2—C1	1.378 (3)
N1—C4	1.420 (2)	C2—H2A	0.9300
N1—H1A	0.8600	C10—C11	1.351 (3)
O2—C13	1.3790 (19)	C10—H10A	0.9300
O2—C14	1.424 (2)	C1—C6	1.376 (3)
C7—C9	1.423 (2)	C1—H1B	0.9300
C7—C13	1.429 (2)	C11—H11A	0.9300
C13—C12	1.360 (2)	C6—H6A	0.9300
C9—C8	1.409 (2)	C14—H14A	0.9600
C9—C10	1.414 (2)	C14—H14B	0.9600
C15—N2	1.151 (2)	C14—H14C	0.9600
C8—H8A	0.9300

O1—Mn1—O1ⁱ	180.0	C5—C4—C3	120.42 (16)
O1—Mn1—N2	90.41 (5)	C5—C4—N1	118.22 (14)
O1ⁱ—Mn1—N2	89.59 (5)	C3—C4—N1	121.36 (15)
O1—Mn1—N2ⁱ	89.59 (5)	C2—C3—C4	119.02 (17)
O1ⁱ—Mn1—N2ⁱ	90.41 (5)	C2—C3—H3A	120.5
N2—Mn1—N2ⁱ	180.00 (7)	C4—C3—H3A	120.5
O1—Mn1—O2	74.23 (4)	C13—C12—C11	120.51 (16)
O1ⁱ—Mn1—O2	105.77 (4)	C13—C12—H12A	119.7
N2—Mn1—O2	88.99 (6)	C11—C12—H12A	119.7
N2ⁱ—Mn1—O2	91.01 (6)	C4—C5—C6	119.83 (16)
O1—Mn1—O2ⁱ	105.77 (4)	C4—C5—H5A	120.1
O1ⁱ—Mn1—O2ⁱ	74.23 (4)	C6—C5—H5A	120.1
N2—Mn1—O2ⁱ	91.01 (6)	C1—C2—C3	120.86 (17)
N2ⁱ—Mn1—O2ⁱ	88.99 (6)	C1—C2—H2A	119.6
O2—Mn1—O2ⁱ	180.00 (5)	C3—C2—H2A	119.6
C7—O1—Mn1	116.71 (9)	C15—N2—Mn1	175.35 (17)
C8—N1—C4	126.92 (14)	C11—C10—C9	120.88 (16)
C8—N1—H1A	116.5	C11—C10—H10A	119.6
C4—N1—H1A	116.5	C9—C10—H10A	119.6
C13—O2—C14	119.03 (14)	C6—C1—C2	119.66 (18)
C13—O2—Mn1	114.02 (9)	C6—C1—H1B	120.2
C14—O2—Mn1	126.09 (12)	C2—C1—H1B	120.2
O1—C7—C9	122.31 (14)	C10—C11—C12	120.05 (17)
O1—C7—C13	121.33 (14)	C10—C11—H11A	120.0
C9—C7—C13	116.36 (14)	C12—C11—H11A	120.0
C12—C13—O2	124.73 (15)	C1—C6—C5	120.20 (18)
C12—C13—C7	121.84 (15)	C1—C6—H6A	119.9
O2—C13—C7	113.42 (14)	C5—C6—H6A	119.9
C8—C9—C10	118.78 (15)	O2—C14—H14A	109.5
C8—C9—C7	120.86 (15)	O2—C14—H14B	109.5
C10—C9—C7	120.35 (15)	H14A—C14—H14B	109.5
N2—C15—S1	178.24 (18)	O2—C14—H14C	109.5
N1—C8—C9	125.08 (14)	H14A—C14—H14C	109.5
N1—C8—H8A	117.5	H14B—C14—H14C	109.5
C9—C8—H8A	117.5

N2—Mn1—O1—C7	−84.38 (11)	C13—C7—C9—C8	−179.21 (15)
N2ⁱ—Mn1—O1—C7	95.62 (11)	O1—C7—C9—C10	179.05 (15)
O2—Mn1—O1—C7	4.46 (10)	C13—C7—C9—C10	−0.2 (2)
O2ⁱ—Mn1—O1—C7	−175.54 (10)	C4—N1—C8—C9	−179.22 (15)
O1—Mn1—O2—C13	−4.72 (10)	C10—C9—C8—N1	−179.53 (16)
O1ⁱ—Mn1—O2—C13	175.28 (10)	C7—C9—C8—N1	−0.5 (3)
N2—Mn1—O2—C13	85.99 (11)	C8—N1—C4—C5	−172.09 (16)
N2ⁱ—Mn1—O2—C13	−94.01 (11)	C8—N1—C4—C3	8.3 (3)
O1—Mn1—O2—C14	−173.90 (17)	C5—C4—C3—C2	1.1 (3)
O1ⁱ—Mn1—O2—C14	6.10 (17)	N1—C4—C3—C2	−179.25 (16)
N2—Mn1—O2—C14	−83.19 (17)	O2—C13—C12—C11	−178.46 (16)
N2ⁱ—Mn1—O2—C14	96.81 (17)	C7—C13—C12—C11	0.8 (3)
Mn1—O1—C7—C9	176.96 (11)	C3—C4—C5—C6	−1.3 (3)
Mn1—O1—C7—C13	−3.79 (19)	N1—C4—C5—C6	179.06 (16)
C14—O2—C13—C12	−6.3 (3)	C4—C3—C2—C1	−0.3 (3)
Mn1—O2—C13—C12	−176.32 (13)	C8—C9—C10—C11	179.98 (17)
C14—O2—C13—C7	174.40 (17)	C7—C9—C10—C11	1.0 (3)
Mn1—O2—C13—C7	4.39 (17)	C3—C2—C1—C6	−0.5 (3)
O1—C7—C13—C12	−179.92 (15)	C9—C10—C11—C12	−0.9 (3)
C9—C7—C13—C12	−0.6 (2)	C13—C12—C11—C10	0.0 (3)
O1—C7—C13—O2	−0.6 (2)	C2—C1—C6—C5	0.3 (3)
C9—C7—C13—O2	178.68 (13)	C4—C5—C6—C1	0.6 (3)
O1—C7—C9—C8	0.1 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.97	2.6501 (16)	135

Experimental details

Crystal data
Chemical formula	[Mn(NCS)₂(C₁₄H₁₃NO₂)₂]
M_r	625.61
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.0204 (2), 9.3070 (2), 9.4087 (2)
α, β, γ (°)	87.417 (1), 82.010 (1), 65.693 (1)
V (Å³)	712.81 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.29 × 0.17 × 0.05

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.877, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	9483, 2509, 2233
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.077, 1.06
No. of reflections	2509
No. of parameters	188
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.24

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.97	2.6501 (16)	134.8

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, H.-Q., Xian, H.-D., Liu, J.-F. & Zhao, G.-L. (2008). Acta Cryst. E64, m1593–m1594. Web of Science CrossRef IUCr Journals Google Scholar
Liu, J.-F., Liu, J.-L. & Zhao, G.-L. (2009). Acta Cryst. E65, m1385–m1386. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xian, H.-D., Liu, J.-F., Li, H.-Q. & Zhao, G.-L. (2008). Acta Cryst. E64, m1422. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, G.-L., Shi, X. & Ng, S. W. (2007). Acta Cryst. E63, m267–m268. CSD CrossRef IUCr Journals Google Scholar
Zhao, G.-L., Zhang, P.-H. & Feng, Y.-L. (2005). Chin. J. Inorg. Chem. 21, 421–424. CAS Google Scholar

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Volume 67| Part 4| April 2011| Page m463

doi:10.1107/S1600536811009330

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